Hacker News Reader

It won't be easy to sail in anything resembling a straight line through the Drake Passage unless your ship is very big.

Speaking of big ships, you might also want to avoid icebergs.

For the land route a realistic approach would be to plot major checkpoints along the true great circle path and just navigate between those checkpoints in whatever way (preferably on land) is most feasible. That would still be interesting.

Yeah I was thinking about how hard it would be to stay “true” to the path as possible if a race or challenge was by wind power only. Also in competition, points could be given or taken based on the amount of deviation from the line etc.